Director, Go-To-Market Enablement

Meet Upside

We created Upside to transform brick-and-mortar commerce. Our technology uses the sophistication of online retail—profit measurement, attribution, and incrementality—to provide users with more value on their everyday purchases and brick-and-mortar businesses with new, profitable customers. We’ve helped millions of users earn 2 to 3 times more cashback than any other product, and hundreds of thousands of brick-and-mortar businesses earn measurable profit. Billions of dollars in commerce run through the Upside platform every year, and that value goes directly back to our retailer partners, the consumers they serve, and important sustainability initiatives.

The Impact You’ll Make

As Director, GTM Enablement you will lead the GTM Training & Enablement function at Upside, developing programs to maximize the effectiveness of our Retailer GTM organization. You will help build alignment between our go-to-market strategies and sales execution and customer retention efforts. The remit covers the entire retailer lifecycle, from demand gen to churn saves and win-back opportunities; from onboarding to ongoing product and pitch certifications. Through these efforts, you will increase productivity across commercial teams and implement best practices that lead to increased revenue, bookings attainment, and customer retention. You will frequently move between strategic, executive-level visioning and producing hands-on, tangible output. You will report into the VP, GTM Strategy & Operations.

• Define and implement annual and quarterly Enablement priorities, ensuring alignment with RGTM leadership on needs and measures of success.
• Manage a team of Enablement professionals, and provide a motivating and clear vision for the future of the team.
• Facilitate and deliver GTM trainings
• Design and manage programs that enable the revenue team to achieve its potential and exceed bookings, revenue, and retention targets, from onboarding new team members to refreshers for experienced sellers and account managers.
• Collaborate with revenue leadership to identify skills gaps across the RGTM team, and build strategies to close those gaps.
• Lead education of the sales and accounts teams on all product initiatives, in partnership with Product Marketing.
• Develop the capabilities of the sales and accounts teams through the design and implementation of sales skills development programs. Source and manage relationships with 3P vendors, to deliver those programs.
• Lead content development, facilitation, and project management of RGTM Kick-off and other commercial team quarterly on-sites throughout the year.
• Define the strategy for Merchant Education, ensuring that Upside is continuing to engage customers in a compelling way that creates increased retention. This will include partnering with our Account Management and Customer Marketing teams to ensure merchants’ sustained, understanding of the value that Upside brings to their businesses.
• Enhance Enablement project management processes (including project plans, dashboards, and templates) that increase efficiency in project execution.
• Design and deliver measurement framework for Enablement programs, reporting periodically to RGTM leadership on the impact of those programs.
• Partner with Sales Ops to source, implement, maintain, and train on technologies that support Enablement efforts.
  
  

What You Should Have

• 10+ years of training & enablement experience
• 5+ years of people management experience
• 5+ years of experience running commercial team off-sites and kickoff events
• Start-up / scale-up experience
• Experience with Challenger or similar sales methodology
• Experience sourcing and partnering with third-party training & enablement vendors
• 5+ years of experience with Highspot, Gong, Outreach.io or equivalent training & enablement / sales tech tools
• Ability to manage internal stakeholders from senior leadership to junior talent
• Bachelor’s degree or higher
  
  

Location:

This hybrid role is required to work at our DC or NYC office for 2 days/week.

Compensation

The US base salary range for this full-time position is $188,100 - $207,900 + bonus (for certain roles) + equity + benefits. The final starting pay will be determined based on job-related skills, experience, qualifications, work location, and market conditions. Your recruiter can share more about the specific salary range during the hiring process.

Benefits

• Medical, dental, and vision coverage starting on Day 1
• Equity (ISOs)
• 401(k) program
• Family planning programs + generous paid parental leave
• Physical fitness and wellness memberships
• Emotional and mental health support programs
• Unlimited PTO + 10 federal holidays + our annual, week-long Winter Break
• Flexible work environment + support for your home office setup
• Lunch and parking reimbursement for in-office employees
• Employee Resource Groups
• Learning and Development opportunities
• Transparent culture
• Amazing mission!
  
  

Why Join Upside?

Our mission, values, and dedication to inclusivity guide our team of more than 300 people worldwide, and the quality of our culture is reflected in the impact we’ve had on the people and businesses we work with. But don’t just take our word for it! In 2023, Upside was included as a Top Workplace in the USA, received six Best Places to Work awards from Built In, was named a Top Workplace for Perks & Culture by The Muse, and was listed second year in a row on the Deloitte Fast 500.

At Upside, we believe that diversity drives innovation. Our differences are what make us stronger. We‘re passionate about building a workplace that represents a variety of backgrounds, skills, and perspectives and we do not discriminate based on race, religion, color, national origin, gender, sexual orientation, age, marital status, veteran status, or disability status. Everyone is welcome here!

Notice To Recruiters And Placement Agencies

This is an in-house search with a dedicated recruiter. Please do not submit resumes to any person or email address at Upside. Upside is not liable for, and will not pay, placement fees for candidates submitted by any party or agency other than its approved recruitment partners.